Fluorosilicon nitrile compounds

ABSTRACT

Novel fluorosilicon nitrile compounds, and methods of preparing them, are described. The fluorosilicon nitrile compounds are characterized by having a total of four substituents attached to a silicon atom, wherein one or two of the substituents are fluorine atoms, one or two of the substituents are cyanoalkyl groups, which are the same as or different from each other, and the remainder of the substituents, if any, are alkyl groups, which are the same as or different from each other.

This present application is the divisional of prior U.S. applicationSer. No. 15/506,330 filed Feb. 24, 2017 which was a national phase under35 USC § 371 of prior PCT International Application NumberPCT/US2015/045599 filed Aug. 18, 2015 which designated the United Statesof America and claimed priority to U.S. Provisional Patent ApplicationSer. No. 62/042,292 filed Aug. 27, 2014.

FIELD OF THE INVENTION

The present invention pertains to novel fluorosilicon nitrile compoundsand methods for their preparation.

DISCUSSION OF THE RELATED ART

Fluorosilicon nitrite compounds containing one or two fluorine atomsattached to a silicon atom as well as at least one cyanoalkyl groupattached to the silicon atom may be used in applications such as batteryfabrication (as solvents or additives, for example), semiconductordeposition, fluorosilicone glass formation, and semiconductor etchingagents. The synthesis of new fluorosilicon compounds of this type wouldtherefore be of great interest, since such new compounds may have uniqueand varied properties as compared to known fluorosilicon nitrilecompounds.

BRIEF SUMMARY OF THE INVENTION

One aspect of the present invention provides novel fluorosilicon nitrilecompounds, wherein the fluorosilicon nitrile compound has a total offour substituents attached to a silicon atom and wherein one or two ofthe substituents are fluorine atoms, one or two of the substituents arecyanoalkyl groups, which are the same as or different from each other(when two cyanoalkyl groups are present), and the remainder of the foursubstituents, if any, are alkyl groups, which are the same as ordifferent from each other (when two alkyl groups are present); subjectto the proviso that the fluorosilicon nitrile compound is notSiF₂(CH₃)(CH₂CH₂CH(CN)CH₃); SiF₂(CH₃)(CH₂CH₂CH₂CN);SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); or SiF₂[CH₂CH(CH₃)CH₂CN]₂.

Also provided by the present invention are fluorosilicon nitritecompounds of general formula Si(R¹)(R²)(R³)(R⁴), wherein one or two ofR¹-R⁴ are fluorine atoms, one or two of R¹-R⁴ are cyanoalkyl groups,which are the same as or different from each other where two cyanoalkylgroups are present, and the remaining R¹-R⁴, if any, are alkyl groups;subject to the proviso that the fluorosilicon nitrile compound is notSiF₂(CH₃)(CH₂CH₂CH(CN)CH₃); SiF₂(CH₃)(CH₂CH₂CH₂CN);SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); or SiF₂[CH₂CH(CH₃)CH₂CN]₂.

In another aspect of the invention, a method of making a fluorosiliconnitrite compound in accordance with the foregoing description isprovided, wherein the method comprises reacting a chlorosilicon nitrilecompound, the chlorosilicon nitrite compound having a total of foursubstituents attached to a silicon atom, wherein one or two of thesubstituents are chlorine atoms, one or two of the substituents arecyanoalkyl groups, which may be the same as or different from eachother, and the remainder of the substituents, if any, are alkyl groups,which are the same as or different from each other, with a fluorinatingagent under conditions effective to exchange fluorine atoms for thechlorine atom(s) in the chlorosilicon nitrile compound.

Still another aspect of the invention provides a method of making afluorosilicon nitrite compound in accordance with the foregoingdescription, wherein the method comprises hydrosilylation of an alkene,especially a cyanoalkene, with a fluoroalkylsilane.

DETAILED DESCRIPTION OF CERTAIN EMBODIMENTS OF THE INVENTION

A fluorosilicon nitrite compound in accordance with the presentinvention has a total of four substituents attached to a silicon atom,wherein one or two of the substituents are fluorine atoms, one or two ofthe substituents are cyanoalkyl groups, which are the same as ordifferent from each other, and the remainder of the substituents, ifany, are alkyl groups, which are the same as or different from eachother. However, the following fluorosilicon nitrite compounds, which areknown compounds, are not considered to be within the scope of thepresent invention: SiF₂(CH₃)(CH₂CH₂CH(CN)CH₃); SiF₂(CH₃)(CH₂CH₂CH₂CN);SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); and SiF₂[CH₂CH(CH₃)CH₂CN]₂.

In one embodiment of the invention, one substituent attached to thesilicon atom is a fluorine atom, one substituent is a cyanoalkyl group,and two substituents are alkyl groups, which are the same as ordifferent from each other.

In another embodiment of the invention, two substituents attached to thesilicon atom are fluorine atoms, one substituent is a cyanoalkyl group,and one substituent is an alkyl group.

According to another embodiment, one substituent attached to the siliconatom is a fluorine atom, two substituents are cyanoalkyl groups, whichare the same as or different from each other, and one substituent is analkyl group.

In still another embodiment of the invention, two substituents attachedto the silicon atom are fluorine atoms and two substituents arecyanoalkyl groups, which are the same as or different from each other.

The cyanoalkyl group or groups attached to the silicon atom may be C2-C9cyanoalkyl groups, in one aspect of the invention. If two cyanoalkylgroups are present, they may be the same as or different from eachother. The alkyl radical bearing one or more cyano (—CN) groups in thecyanoalkyl group may be a straight chain, branched, oralicyclic-containing alkyl radical. Each cyanoalkyl group may containone, two or more cyano groups per cyanoalkyl group. Each cyano group maybe substituted, for example, at a terminal position of an alkyl radicalor at an internal position of an alkyl radical. For example, where thealkyl radical is a straight chain C4 alkyl radical, a cyano group may besubstituted at the terminal position to provide the cyanoalkyl group—CH₂CH₂CH₂CH₂CN or at an internal position to provide one of thefollowing cyanoalkyl groups: —CH(CN)CH₂CH₂CH₃; —CH₂CH(CN)CH₂CH₃;—CH₂CH₂CH(CN)CH₃.

Suitable cyanoalkyl groups may, for example, be selected from the groupconsisting of:

-   -   —CH₂CH(CN)CH₃;    -   —CH(CN)CH₂CH₃;    -   —C(CN)(CH₃)₂;    -   —CH₂CH₂CN;    -   —CH(CN)CH₃;    -   —CH₂CH₂CH(CN)CH₃;    -   —CH₂CH(CN)CH₂CH₃;    -   —(CH₂)₃CN;    -   —(CH₂)₂CN;    -   —(CH₂)₄CN;    -   —(CH₂)₅CN;    -   —(CH₂)₃C(CH₃)₂CN;    -   —CH(CH₃)CH₂CN;    -   —CH(CN)CH(CN)CH₃;    -   —C(CN)(CH₃)CH₂CN;    -   —CH(CH₂CN)₂;    -   —CH(CN)CH₂CH₂CN;    -   —CH(CH₃)CH(CN)₂;    -   —C(CN)₂(CH₂CH₃);    -   —CH₂CH(CN)CH₂CN;    -   —C(CN)(CH₃)CH₂CN;    -   —CH(CH₂CH₃)CH₂CN;    -   —CH(CN)CH₂CH₂CH₃;    -   —CH(CH₃)CH₂CH₂CN;    -   —CH(CH₂CN)CH₂CH₃;    -   —CH(CH₃)CH(CH)CH₃;    -   —C(CN)(CH₃)CH₂CH₃;    -   —CH₂CH(CN)CH₂CH₃;    -   —CH₂CH(CH₃)CH₂CN;    -   —C(CH₃)₂CH₂CN;    -   —CH(CN)CH(CH₃)₂;    -   —CH₂CH₂CH(CN)CH₃;    -   —CH₂CH(CH₂CN)CH₂CH₃;    -   —C(CH₃)(CH₂CH₃)CH₂CN;    -   —CH₂CH₂CH(CN)CH₂CH₃;    -   —CH(CH₃)CH(CN)CH₂CH₃;    -   —CH₂CH₂CH₂CH(CN)CH₃;    -   —CH(CH₃)CH₂CH(CN)CH₃;    -   —C(CH₂CH₃)₂(CN);    -   —CH₂CH₂CH(CH₃)CH₂CN;    -   —CH(CH₃)CH(CH₃)CH₂CN;    -   —(CH₂)₂C(CH₃)₂CN;    -   —CH(CH₃)C(CH₃)₂CN;    -   —CH(CH₂CH₃)CH(CN)CH₃;    -   —CH₂CH(CH₃)CH₂CH₂CN;    -   —C(CH₃)₂CH₂CH₂CN;    -   —CH(CH₂CH₃)CH₂CH₂CN;    -   —CH(CH₂CN)CH₂CH₂CH₃;    -   —CH(CN)CH₂CH₂CH₂CH₃;    -   —CH(CH₃)CH₂CH₂CH₂CN;    -   —C(CH₃)₂CH(CN)CH₃;    -   —C(CH₃)(CN)CH(CH₃)₂;    -   —CH(CH₂CN)CH(CH₃)₂;    -   —CH₂CH(CN)CH₂CH₂CH₃;    -   —C(CH₃)(CN)CH₂CH₂CH₃;    -   —CH₂CH(CN)CH(CH₃)₂;    -   —CH(CN)CH₂CH₂CH₂CH₃;    -   —CH₂CH(CH₃)CH(CN)CH₃;    -   —CH(CN)CH₂CH(CH₃)₂;    -   —CH(CN)CH(CH₃)CH₂CH₃;    -   —C(CH₃)(CN)CH(CN)CH₂CH₃;    -   —C(CN)(CH₂CH₃)CH(CN)CH₃;    -   —CH(CH₂CN)CH₂CH₂CH₂CN;    -   —CH(CN)CH₂CH₂CH₂CH₂CN;    -   —CH₂CH(CN)CH₂CH₂CH₂CN;    -   —C(CH₃)(CN)CH₂CH₂CH₂CN;    -   —C(CH₃)(CH₂CH₃)CH(CN)₂;    -   —C(CN)₂CH(CH₃)CH₂CH₃;    -   —C(CN)₂CH₂CH(CH₃)₂;    -   —CH(CH(CN)₂)CH(CH₃)₂;    -   —C(CN)(CH₂CH₃)CH₂CH₂CN;    -   —CH(CH₃)CH(CN)CH₂CH₂CN;    -   —CH₂CH(CN)CH₂CH(CN)CH₃;    -   —C(CN)(CH₃)CH₂CH(CN)CH₃;    -   —(CH₂)₃CH(CN)CH₂CN;    -   —CH(CH₃)CH₂CH(CN)CH₂CN;    -   —CH(CH₂CH₃)CH(CN)CH₂CN;    -   —C(CN)(CH₂CN)CH₂CH₂CH₃;    -   —C(CH₃)₂CH(CN)CH₂CN;    -   —C(CN)(CH₂CN)CH(CH₃)₂;    -   —C(CH₃)(CH₂CN)CH₂CH₂CN;    -   —CH(CH₂CN)CH(CH₃)CH₂CN;    -   —CH₂CH(CH₂CN)CH₂CH₂CN;    -   —CH₂CH(CH₂CN)CH(CN)CH₃;    -   —C(CH₃)(CH₂CN)CH(CN)CH₃;    -   —CH(CH(CN)₂)CH₂CH₂CH₃;    -   —C(CN)₂CH₂CH₂CH₂CH₃;    -   —CH(CH₂CN)CH₂CH(CN)CH₃;    -   —CH(CH₂CH₂CN)CH(CN)CH₃;    -   —CH(CH₃)CH₂CH₂CH(CN)₂;    -   —CH(CH₂CH₃)CH₂CH(CN)₂;    -   —CH₂CH(CH₃)CH₂CH(CN)₂;    -   —C(CH₃)₂CH₂CH(CN)₂;    -   —CH₂CH₂CH₂C(CN)₂CH₃;    -   —CH(CH₃)CH₂C(CN)₂CH₃;    -   —CH(CH(CN)₂)CH(CH₃)₂;    -   —CH₂CH₂CH(CH₃)CH(CN)₂;    -   —CH(CH₃)CH(CH₃)CH(CN)₂; and    -   —CH₂CH₂CH₂CH₂CH(CN)₂ and combinations thereof, where the        fluorosilicon nitrile compound contains two cyanoalkyl groups        per molecule.

When at least one alkyl group is present in the fluorosilicon nitrilecompound as a substituent attached to the silicon atom, the alkyl groupmay, for example, be a C1-C8 alkyl group. The alkyl group may bestraight chain or branched or may contain a cyclic structure (i.e., thealkyl group may be alicyclic). If two alkyl groups are attached to thesilicon atom, they may be the same as each other or different from eachother. Suitable alkyl groups include, for example, methyl, ethyl,n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl,n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl andisomers thereof, and n-octyl and isomers thereof.

In one aspect of the invention, the fluorosilicon nitrile compoundcontains, as substituents attached to the silicon atom, one fluorineatom, one cyanoalkyl group, and two C1-C8 alkyl groups, which are thesame as or different from each other. In another aspect of theinvention, the fluorosilicon nitrile compound contains, as substituentsattached to the silicon atom, two fluorine atoms, one cyanoalkyl groupand one C1-C8 alkyl group. In these embodiments, the C1-C8 alkyl groupsmay, for example, be selected from the group consisting of methyl,ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyland combinations thereof.

A further embodiment of the invention provides a fluorosilicon nitrilecompound of general formula Si(R¹)(R²)(R³)(R⁴), wherein one or two ofR¹-R⁴ are fluorine atoms, one or two of R¹-R⁴ are cyanoalkyl groups,which are the same as or different from each other where two cyanoalkylgroups are present, and the remaining R¹-R⁴, if any, are alkyl groups;subject to the proviso that the fluorosilicon nitrile compound is notSiF₂(CH₃)(CH₂CH₂CH(CN)CH₃); SiF₂(CH₃)(CH₂CH₂CH₂CN);SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); or SiF₂[CH₂CH(CH₃)CH₂CN]₂. The alkyl groupsand cyanoalkyl groups may be any of such groups described previously.

For example, R¹ and R² may both be F, R³ may be an alkyl group and R⁴may be a cyanoalkyl group. Alternatively, R¹ and R² may both be F and R³and R⁴ may both be cyanoalkyl groups. In yet another aspect, R1 may beF, R² and R³ may both be alkyl, and R⁴ may be cyanoalkyl. Additionally,in a further aspect of the invention, R¹ may be F, R² may be alkyl, andR³ and R⁴ may both be cyanoalkyl.

Examples of fluorosilicon nitrile compounds in accordance with thepresent invention are shown in Table I. Each of these compounds may besynthesized from known chlorosilicon nitrile compounds containing Clatoms, rather than F atoms, substituted on the silicon atom, using thefluorination methods described elsewhere herein.

TABLE I Empirical Compound # Structure Formula  1

C₆H₁₂NSiF  2

C₅H₉NSiF₂  3

C₅H₉NSiF₂  4

C₅H₉NSiF₂  5

C₅H₉NSiF₂  6

C₇H₁₄NSiF  7

C₇H₁₄NSiF  8

C₇H₁₄NSiF  9

C₈H₁₂N₂SiF₂ 10

C₇H₁₁N₂SiF 11

C₇H₁₁N₂SiF 12

C₆H₈N₂SiF₂ 13

C₉H₁₈NSiF 14

C₈H₁₅NSiF₂ 15

C₁₀H₂₀NSiF 16

C₆H₁₁NSiF₂

Additional exemplary fluorosilicon nitrile compounds illustrative of thepresent invention are shown in Table II. These compounds contain one ortwo fluorine atoms attached to a silicon atom, a cyanoalkyl groupattached to the silicon atom, and one or two methyl groups attached tothe silicon atom. Also within the scope of the present invention arefluorosilicon compounds homologous or analogous to those shown in TableII in which the methyl group (in the case of the difluoromethylsiliconnitriles) or one or both of the methyl groups (in the case of thefluorodimethylsilicon nitriles) is or are substituted by an alkyl groupother than methyl, in particular a branched or straight chain C2-C8alkyl group such as ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl,iso-butyl, tert-butyl and the like.

TABLE II Compound Fluorodimethylsilicon Difluoromethylsilicon # NitrileNitrile 21

21a = C₆H₁₂NSiF 21b = C₅H₉NSiF₂

21c = C₆H₁₂NSiF 21d = C₅H₉NSiF₂ 22

22a =C₇H₁₁N₂SiF 22b = C₆H₈N₂SiF₂

22c = C₇H₁₁N₂SiF 22d = C₆H₈N₂SiF₂ 23

23a = C₇H₁₁N₂SiF 23b = C₆H₈N₂SiF₂

23c = C₇H₁₁N₂SiF 23d =C₆H₈N₂SiF₂ 24

24a = C₇H₁₁N₂SiF 24b = C₆H₈N₂SiF₂

24c = C₇H₁₁N₂SiF 24d = C₆H₈N₂SiF₂ 25

25a = C₇H₁₁N₂SiF 25b = C₆H₈N₂SiF₂

25c = C₇H₁₁N₂SiF 25d = C₆H₈N₂SiF₂ 26

26a = C₇H₁₄NSiF 26b = C₆H₁₁NSiF₂

26c = C₇H₁₄NSiF 26d = C₆H₁₁NSiF₂ 27

27a = C₇H₁₄NSiF 27b = C₆H₁₁NSiF₂

27c = C₇H₁₄NSiF 27d = C₆H₁₁NSiF₂ 28

28a = C₇H₁₄NSiF 28b = C₆H₁₁NSiF₂

28c = C₇H₁₄NSiF 28d = C₆H₁₁NSiF₂ 29

29a = C₇H₁₄NSiF 29b = C₆H₁₁NSiF₂

29c = C₇H₁₄NSiF 29d = C₆H₁₁NSiF₂ 30

30a = C₇H₁₄NSiF 30b = C₆H₁₁NSiF₂ 31

31a = C₇H₁₄NSiF

31b = C₇H₁₄NSiF 31c = C₆H₁₁NSiF₂ 32

32a = C₇H₁₄NSiF 32b = C₆H₁₁NSiF₂ 33

33 = C₇H₁₄NSiF 34

34a = C₈H₁₆NSiF 34b = C₇H₁₃NSiF₂

34c = C₈H₁₆NSiF 34d = C₇H₁₃NSiF₂ 35

35a = C₈H₁₆NSiF 35b = C₇H₁₃NSiF₂

35c = C₈H₁₆NSiF 35d = C₇H₁₃NSiF₂ 36

36a = C₈H₁₆NSiF 36b = C₇H₁₃NSiF₂

36c = C₈H₁₆NSiF 36d = C₇H₁₃NSiF₂ 37

37a = C₈H₁₆NSIF 37b = C₇H₁₃NSiF₂ 38

38a = C₈H₁₆NSiF 38b = C₇H₁₃NSiF₂

38c = C₈H₁₆NSiF 38d = C₇H₁₃NSiF₂ 39

39a = C₈H₁₆NSiF 39b = C₇H₁₃NSiF₂

39c = C₈H₁₆NSiF 39d = C₇H₁₃NSiF₂ 40

40a = C₈H₁₆NSiF 40b = C₇H₁₃NSiF₂ 41

41a = C₈H₁₆NSiF 41b = C₇H₁₃NSiF₂

41c = C₈H₁₆NSiF 41d = C₇H₁₃NSiF₂ 42

42a = C₈H₁₆NSiF 42b = C₇H₁₃NSiF₂

42c = C₈H₁₆NSiF 42d = C₇H₁₃NSiF₂ 43

43a = C₈H₁₆NSiF 43b = C₇H₁₃NSiF₂ 44

44a = C₈H₁₆NSiF 44b = C₇H₁₃NSiF₂

44c = C₈H₁₆NSiF 44d = C₇H₁₃NSiF₂ 45

45a = C₈H₁₆NSiF 45b = C₇H₁₃NSiF₂

45c = C₈H₁₆NSiF 45d = C₇H₁₃NSiF₂ 46

46a = C₈H₁₆NSiF 46b = C₇H₁₃NSiF₂ 47

47a = C₈H₁₆NSiF 47b = C₇H₁₃NSiF₂

47c = C₈H₁₆NSiF 47d = C₇H₁₃NSiF₂ 48

48a = C₈H₁₆NSiF 48b = C₇H₁₃NSiF₂ 49

49a = C₈H₁₆NSiF 49b = C₇H₁₃NSiF₂ 50

50a = C₈H₁₆NSiF 50b = C₇H₁₃NSiF₂ 51

51a = C₈H₁₆NSiF 51b = C₇H₁₃NSiF₂ 52

52a = C₈H₁₆NSiF 52b = C₇H₁₃NSiF₂ 53

53a = C₉H₁₅N₂SiF 53b = C₈H₁₂N₂SiF₂

53c = C₉H₁₅N₂SiF 53d = C₈H₁₂N₂SiF₂ 54

54a = C₉H₁₅N₂SiF 54b = C₈H₁₂N₂SiF₂

54c = C₉H₁₅N₂SiF 54d = C₈H₁₂N₂SiF₂ 55

55a = C₉H₁₅N₂SiF 55b = C₈H₁₂N₂SiF₂

55c = C₉H₁₅N₂SiF 55d = C₈H₁₂N₂SiF₂ 56

56a = C₉H₁₅N₂SiF 56b = C₈H₁₂N₂SiF₂

56c = C₉H₁₅N₂SiF 56d = C₈H₁₂N₂SiF₂ 57

57a = C₉H₁₅N₂SiF 57b = C₈H₁₂N₂SiF₂

57c = C₉H₁₅N₂SiF 57d = C₈H₁₂N₂SiF₂ 58

58a = C₉H₁₅N₂SiF 58b = C₈H₁₂N₂SiF₂

58c = C₉H₁₅N₂SiF 58d = C₈H₁₂N₂SiF₂ 59

59a = C₉H₁₅N₂SiF 59b = C₈H₁₂N₂SiF₂

59c = C₉H₁₅N₂SiF 59d = C₈H₁₂N₂SiF₂ 60

60a = C₉H₁₅N₂SiF 60b = C₈H₁₂N₂SiF₂

60c = C₉H₁₅N₂SiF 60d = C₈H₁₂N₂SiF₂ 61

61a = C₉H₁₅N₂SiF 61b = C₈H₁₂N₂SiF₂ 62

62a = C₉H₁₅N₂SiF 62b = C₈H₁₂N₂SiF₂ 63

63a = C₉H₁₅N₂SiF 63b = C₈H₁₂N₂SiF₂

63c = C₉H₁₅N₂SiF 63d = C₈H₁₂N₂SiF₂ 64

64a = C₉H₁₅N₂SiF 64b = C₈H₁₂N₂SiF₂

64c = C₉H₁₅N₂SiF 64d = C₈H₁₂N₂SiF₂ 65

65a = C₉H₁₅N₂SiF 65b = C₈H₁₂N₂SiF₂ 66

66a = C₉H₁₅N₂SiF 66b = C₈H₁₂N₂SiF₂

66c = C₉H₁₅N₂SiF 66d = C₈H₁₂N₂SiF₂ 67

67a = C₉H₁₅N₂SiF 67b = C₈H₁₂N₂SiF₂

67c = C₉H₁₅N₂SiF 67d = C₈H₁₂N₂SiF₂ 68

681 = C₉H₁₅N₂SiF 68b = C₈H₁₂N₂SiF₂

68c = C₉H₁₅N₂SiF 68d = C₈H₁₂N₂SiF₂ 69

69a = C₉H₁₅N₂SiF 69b = C₈H₁₂N₂SiF₂

69c = C₉H₁₅N₂SiF 69d = C₈H₁₂N₂SiF₂ 70

70a = C₉H₁₅N₂SiF 70b = C₈H₁₂N₂SiF₂

70c = C₉H₁₅N₂SiF 70d = C₈H₁₂N₂SiF₂ 71

71a = C₉H₁₅N₂SiF 71b = C₈H₁₂N₂SiF₂

71c = C₉H₁₅N₂SiF 71d = C₈H₁₂N₂SiF₂ 72

72a = C₉H₁₅N₂SiF 72b = C₈H₁₂N₂SiF₂ 73

73a = C₉H₁₅N₂SiF 73b = C₈H₁₂N₂SiF₂

73c = C₉H₁₅N₂SiF 73d = C₈H₁₂N₂SiF₂ 74

74a = C₉H₁₅N₂SiF 74b = C₈H₁₂N₂SiF₂

Also provided by the present invention are methods of making theabove-mentioned fluorosilicon nitrile compounds.

In one aspect of the invention, a method is provided which comprisesreacting a chlorosilicon nitrile compound with a fluorinating agentunder conditions effective to exchange fluorine atoms for the chlorineatoms in the chlorosilicon nitrile compound. The chlorosilicon nitrilecompound has a total of four substituents attached to a silicon atom,wherein one or two of the substituents are chlorine atoms, one or two ofthe substituents are cyanoalkyl groups, which may be the same as ordifferent from each other, and the remainder of the substituents, ifany, are alkyl groups, which are the same as or different from eachother. The chlorosilicon nitrile compound may correspond to generalformula Si(R¹)(R²)(R³)(R⁴), wherein one or two of R¹-R⁴ are chlorineatoms, one or two of R¹-R⁴ are cyanoalkyl groups, which are the same asor different from each other where two cyanoalkyl groups are present,and the remaining R¹-R⁴, if any, are alkyl groups.

The fluorinating agent may, for example, be selected from the groupconsisting of HF, MF, MHF₂ and SbF₃, where M is Na, K, Rb, Cs or NH₄.Fluorides of antimony, zinc, lead, mercury, silver, cobalt, copper,tungsten and other metals may be utilized as the fluorinating agent.Sodium fluoroborate may also be used, as can mixtures of SbF₃ and BF₃ orNaF and sulfuric acid. Other suitable fluorinating agents include neatBF₃, BF₃ etherates, Na₂SiF₆, NaPF₆, NaSbF₆, NaBF₄, Me₃SnF, PF₅, PhCBF₄,NOBF₄, and NO₂BF₄. If HF (hydrogen fluoride) is employed, it may be usedin anhydrous form or in an aqueous-alcoholic or aqueous medium.Potassium hydrogen difluoride and ammonium hydrogen difluoride (ammoniumbifluoride) are especially useful fluorinating agents.

Certain of the chlorosilicon nitrile compounds useful as the startingmaterial in the aforementioned fluorination reaction are known compoundsthat may be prepared using methods known in the art. Such compoundsinclude, for example, compounds having the following CAS registrationnumbers: 42759-42-2; 59343-99-6; 42759-43-3; 100792-00-5, 1068-40-2;18243-57-7; 1274903-71-7, 876343-97-4; 2617-09-6; 18276-25-0;18135-77-8; 103613-06-5; 1071-17-6; 18727-31-6; 7031-17-6; 169206-21-7;875478-07-2; 161582-95-2; 113641-37-5; and 1186-40-9. Additionalchlorosilicon nitrile compounds may be readily synthesized byhydrosilylation of an alkene with a chloroalkylsilane. In one embodimentof such a synthesis, the alkene is a cyanoalkene. The cyanoalkene maysuitably be a C3-C10 cyanoalkene, for example, and may contain a singlecarbon-carbon double bond and one, two or more cyano (—CN) groups permolecule. The structure of the cyanoalkene is selected so as to providea cyanoalkyl group of the type desired in the fluorosilicon nitrileproduced by hydrosilylation. Illustrative examples of suitablecyanoalkenes include, but are not limited to, CH₃CH═CHCN (CAS4786-20-3); CH₃C(CN)═CHCN (CAS 70240-55-0); NCCH₂CH═CHCN (CAS7717-24-0); CH₃CH═C(CN)₂ (CAS 1508-07-2); CH₂═C(CN)CH₂CN (CAS24412-94-0); CH₃CH₂CH═CHCN (CAS 13284-42-9); CH₂═CHCH₂CH₂CN (CAS592-51-8); CH₃CH═CHCH₂CN (CAS 4635-87-4); CH₃CH═C(CN)CH₃ (CAS4403-61-6); CH₂═C(CN)CH₂CH₃ (CAS 1647-11-6); CH₂═C(CH₃)CH₂CN (CAS4786-19-0); (CH₃)₂C═CHCN (CAS 4786-24-7); CH₂CHCH(CN)CH₃ (CAS16529-56-9); CH₂═C(CH₂CN)CH₂CH₃ (CAS 1462956-36-0); CH₂═CHCH(CN)CH₂CH₃(CAS 180974-28-1); CH₂═CHCH₂CH(CN)CH₃ (CAS 89464-18-6);CH₃CH₂C(CN)═CHCH₃ (CAS 89580-25-6); CH₂CHCH(CH₃)CH₂CN (CAS 51980-04-2);CH₂═CHC(CH₃)₂CN (CAS 41405-16-7); CH₃CH(CN)CH═CHCH₃ (CAS 37674-624);CH₂═C(CH₃)CH₂CH₂CN (CAS 34998-36-2); CH₃CH₂CH═CHCH₂CN (CAS 16170-44-8);CH₃CH₂CH₂CH═CHCN (CAS 5636-69-1); CH₂═CHCH₂CH₂CH₂CN (CAS 5048-19-1);(CH₃)₂C═C(CH₃)CN (CAS 4786-37-2); (CH₃)₂C═CHCH₂CN (CAS 4786-23-6);CH₂═C(CN)CH₂CH₂CH₃ (CAS 3931-57-5); CH₂═C(CN)CH(CH₃)₂ (CAS 2813-69-6);CH₃CH₂CH₂CH═CHCN (CAS 67889-07-0); CH₂C(CH₃)CH(CN)CH₃ (CAS 25653-08-1);(CH₃)₂CHCH═CHCN (CAS 19124-15-3); CH₃CH₂C(CH₃)═CHCN (CAS 14799-77-0);CH₃C(CN)═C(CN)CH₂CH₃ (CAS 1003003-54-0); NCCH₂CH₂CH₂CH═CHCN (CAS872307-67-0); CH₂═C(CN)CH₂CH₂CH₂CN (CAS 856347-40-5);CH₃CH₂C(CH₃)═C(CN)₂ (CAS 13017-50-0); (CH₃)₂CHCH═C(CN)₂ (CAS13134-03-7); CH₃CH═C(CN)CH₂CH₂CN (CAS 22485-88-7); CH₂═C(CN)CH₂CH(CN)CH₃(CAS 35299-21-9); CH₂═CHCH₂CH(CN)CH₂CN (CAS 364453-09-5);CH₃CH═CHCH(CN)CH₂CN (CAS 36453-10-8); CH₃CH₂CH═C(CN)CH₂CN (CAS36453-11-9); (CH₃)₂C═C(CN)CH₂CN (CAS 67386-03-2); NCCH₂C(CH₃)═CHCH₂CN(CAS 76257-96-0); CH₂═C(CH₂CN)CH₂CH₂CN (CAS 80718-20-3);CH₂═C(CH₂CN)CH(CN)CH₃ (CAS 80718-26-9); CH₃CH₂CH₂CH═C(CN)₂ (CAS87948-15-0); CH₃CH(CN)CH═CHCH₂CN (CAS 122917-04-8); (NC)₂CHCH₂CH═CHCH₃(CAS 130575-29-0); CH₂═C(CH₃)CH₂CH(CN)₂ (CAS 145050-18-6);CH₂═CHCH₂C(CN)₂CH₃ (CAS 154657-02-0); (CH₃)₂C═CHCH(CN)₂ (CAS442661-894); CH₂═CHCH(CH₃)CH(CN)₂ (CAS 443124-95-6); andCH₂═CHCH₂CH₂CH(CN)₂ (CAS 475197-78-5).

The chloroalkylsilane may be a silane containing, as substituentsattached to the silicon atom, one or two hydrogen atoms, one chlorineatom and one or two alkyl groups, which may be the same as each other ordifferent from each other. Where one hydrogen atom is present, onemolecule of cyanoalkene reacts with one molecule of chloroalkylsilane inthe hydrosilylation reaction, thereby introducing a single cyanoalkylgroup into the silane. When two hydrogen atoms are present, twomolecules of cyanoalkene react with one molecule of chloroalkylsilane,thereby introducing two cyanoalkyl groups into the silane. In thisembodiment, the chloroalkyl silane may correspond to the generalstructure SiCl(H)_(m)(R)_(3-n), where n is 1 or 2 and R is alkyl. Inanother aspect of the invention, the chloroalkyl silane may be a silanecontaining, as substituents attached to the silicon atom, one or twohydrogen atoms, two chlorine atoms, and, where only one hydrogen atom isattached to silicon, a single alkyl group. In this embodiment, thechloroalkyl silane may correspond to the general structureSiCl₂(H)_(n)(R)_(2-n), where n is 1 or 2 and R, if present, is alkyl.Where one hydrogen atom is present, one molecule of cyanoalkene reactswith one molecule of ehloroalkylsitane in the hydrosilylation reaction,thereby introducing a single cyanoalkyl group into the silane. When twohydrogen atoms are present, two molecules of alkene react with onemolecule of chloroalkylsilane, thereby introducing two cyanoalkyl groupsinto the silane.

The alkyl groups may, for example, be a C1-C8 alkyl group such asmethyl, ethyl, n-propyl, isopropyl, n-butyl and isomers thereof,n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl andisomers thereof, n-octyl and isomers thereof and combinations of suchalkyl groups. The chloroalkylsilane thus may correspond to the generalformula HSi(R¹)(R²)(R³), wherein one or two of R¹-R³ are chlorine atomsand the remaining R¹-R³ are alkyl groups, which may be the same as ordifferent from each other where more than one alkyl group per moleculeis present.

An example of such a synthetic reaction scheme is shown below. In thisexample, the alkene 2-cyanobut-1-ene (CAS #1647-11-6) is hydrosilylatedwith chlorodimethylsilane (CDMS), leading to a chlorosilicon nitritehaving the structure shown (Reaction 1A). The chlorosilicon nitrite isthen reacted with a fluorinating agent to produce fluorosilicon nitritecompound 30a having the structure shown (Reaction 1B).

A further method of making a fluorosilicon nitrite compound inaccordance with the present invention comprises hydrosilylation of analkene with a fluoroalkylsilane (i.e., reacting the alkene andfluoroalkylsilane under hydrosilylation conditions). The reacted alkenemay be a cyanoalkene, for example. Suitable cyanoalkenes include any ofthe previously mentioned cyanoalkenes.

The fluoroalkylsilane may be a silane containing, as substituentsattached to the silicon atom, one or two hydrogen atoms, one fluorineatom and one or two alkyl groups, which may be the same as each other ordifferent from each other. The total number of hydrogen atoms, fluorineatom, and alkyl groups equals four. Where one hydrogen atom attached tosilicon is present, one molecule of cyanoalkene reacts with one moleculeof fluoroalkylsilane in the hydrosilylation reaction, therebyintroducing a single cyanoalkyl group into the silane. When two hydrogenatoms attached to silicon are present, two molecules of cyanoalkenereact with one molecule of fluoroalkylsilane, thereby introducing twocyanoalkyl groups into the silane. In this embodiment, the fluoroalkylsilane may correspond to the general structure SiF(H)_(n)(R)^(3-n),where n is 1 or 2 and R is alkyl. In another aspect of the invention,the fluoroalkyl silane may be a slime containing, as substituentsattached to the silicon atom, one or two hydrogen atoms, two fluorineatoms, and, where only one hydrogen atom is attached to silicon, asingle alkyl group. The total number of hydrogen atoms, fluorine atomsand alkyl group equals four. In this embodiment, the fluoroalkyl silanemay correspond to the general structure SiF₂(H)_(n)(R)_(2-n), where n is1 or 2 and R, if present, is alkyl. Where one hydrogen atom attached tosilicon is present, one molecule of cyanoalkene reacts with one moleculeof fluoroalkylsilane in the hydrosilylation reaction, therebyintroducing a single cyanoalkyl group into the silane. When two hydrogenatoms attached to silicon are present, two molecules of cyanoalkenereact with one molecule of fluoroalkylsilane, thereby introducing twocyanoalkyl groups into the silane.

The alkyl groups may, for example, be a C1-C8 alkyl group such asmethyl, ethyl, n-propyl, isopropyl, n-butyl and isomers thereof,n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl andisomers thereof, n-octyl and isomers thereof and combinations of suchalkyl groups.

The fluoroalkylsilane thus may correspond to the general formulaHSi(R¹)(R²)(R³), wherein one or two of R¹-R³ are fluorine atoms and theremaining R¹-R³ are alkyl groups, which may be the same as or differentfrom each other where more than one alkyl group per molecule is present.

The following reaction scheme (Reaction 1C) is an example of such areaction. In this example, fluorosilicon nitrile compound 30a isprepared by direct hydrosilylation of the alkene 2-cyanobut-1-ene withfluorodimethylsilane (FDMS).

In one embodiment of the invention, the above-mentioned hydrosilylationreactions are carried out in the presence of a hydrosilylation catalyst,in particular an organoplatinum coordination complex having activity asa hydrosilylation catalyst. Karstedt's catalyst, which is anorganoplatinum compound derived from divinyl-containing disiloxane (bytreatment of chloroplatinic acid with divinyltetramethyldisiloxane), isan example of a suitable catalyst for this purpose. Other suitablehydrosilylation catalysts include, for example, Wilkinson's catalyst(tris(triphenylphosphone)rhodium (I) chloride), the cobalt carbonylcomplex Co₂(CO)₈, and H₂PtCl₆(Speier's catalyst). Hydrosilylationtypically proceeds in an anti-Markovnikov manner. However, dependingupon the reaction conditions used, hydrosilylation may not be completelyselective; that is, a mixture of isomeric hydrosilylation products maybe obtained. The individual components of such reaction product mixturesmay be purified and isolated using any conventionally known techniques,such as fractional distillation. Alternatively, the mixture ofcomponents may be utilized for the desired end use without suchfractionation or separation.

Typically, where it is desired to introduce a single cyanoalkyl groupinto a silane, the molar ratio of cyanoalkene to fluoroalkylsilane maybe approximately 1:1, e.g., from about 0.7:1 to about 1.3:1. If it isdesired to introduce two cyanoalkyl groups, the molar ratio ofcyanoalkene to fluoroalkylsilane may be approximately 2:1, e.g., fromabout 1.5:1 to about 15:1. The hydrosilylation may be carried out usingan organic solvent, e.g., an aromatic hydrocarbon, as a reaction medium.The mixture of cyanoalkene, fluoroalkylsilane, hydrosilylation catalystand optional solvent may be heated for a time and at a temperatureeffective to provide the desired conversion of the starting materials.For example, reaction temperatures of from about 50° C. to about 110° C.and reaction times of from about 1 to about 6 hours may be utilized.

Aspects of the present invention include:

-   -   1. A fluorosilicon nitrile compound having a total of four        substituents attached to a silicon atom, wherein one or two of        the substituents are fluorine atoms, one or two of the        substituents are cyanoalkyl groups, which are the same as or        different from each other, and the remainder of the        substituents, if any, are alkyl groups, which are the same as or        different from each other;        -   subject to the proviso that the fluorosilicon nitrile            compound is not SiF₂(CH₃)(CH₂CH₂CH(CN)CH₃);            SiF₂(CH₃)(CH₂CH₂CH₂CN); SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); or            SiF₂[CH₂CH(CH₃)CH₂CN]₂.    -   2. The fluorosilicon nitrile compound of claim 1, wherein one        substitutent is a fluorine atom, one substituent is a cyanoalkyl        group, and two substituents are alkyl groups, which are the same        as or different from each other.    -   3. The fluorosilicon nitrite compound of claim 1, wherein two        substituents are fluorine atoms, one substituent is a cyanoalkyl        group, and one substituent is an alkyl group.    -   4. The fluorosilicon nitrile compound of claim 1, wherein one        substituent is a fluorine atom, two substituents are cyanoalkyl        groups, which are the same as or different from each other, and        one substituent is an alkyl group.    -   5. The fluorosilicon nitrite compound of claim 1, wherein two        substituents are fluorine atoms and two substituents are        cyanoalkyl groups, which are the same as or different from each        other.    -   6. The fluorosilicon nitrite compound of any one of the        preceding claims, wherein the cyanoalkyl groups are C2-C9        cyanoalkyl groups.    -   7. The fluorosilicon nitrile compound of claim 1, wherein at        least one alkyl group is present and the alkyl group is a C1-C8        alkyl group,    -   8. The fluorosilicon nitrite compound of any one of the        preceding claims, wherein the cyanoalkyl group or cyanoalkyl        groups contain(s) a single cyano group per cyanoalkyl group.    -   9. The fluorosilicon nitrite compound of any one of claims 1        through 7, wherein the cyanoalkyl group or cyanoalkyl groups        contain(s) two cyano groups per cyanoalkyl group.    -   10. The fluorosilicon nitrite compound of any one of the        preceding wherein the cyanoalkyl group or cyanoalkyl groups        contain(s) a cyano group which is substituted at a terminal        position of an alkyl radical.    -   11. The fluorosilicon nitrite compound of any one of the        preceding wherein the cyanoalkyl group or cyanoalkyl groups        contain(s) a cyano group which is substituted at an internal        position of an alkyl radical.    -   12. The fluorosilicon nitrile compound of any one of the        preceding claims, wherein the cyanoalkyl group or cyanoalkyl        groups are selected from the group consisting of:        -   —CH₂CH(CN)CH₃;        -   —CH(CN)CH₂CH₃;        -   —C(CN)(CH₃)₂;        -   —CH₂CH₂CN;        -   —CH(CN)CH₃;        -   —CH₂CH₂CH(CN)CH₃;        -   —CH₂CH(CN)CH₂CH₃;        -   —(CH₂)₃CN;        -   —(CH₂)₂CN;        -   —(CH₂)₄CN;        -   —(CH₂)₅CN;        -   —(CH₂)₃C(CN)₂CH₃;        -   —CH(CH₃)CH₂CN;        -   —CH(CN)CH(CN)CH₃;        -   —C(CN)(CH₃)CH₂CN;        -   —CH(CH₂CN)₂;        -   —CH(CN)CH₂CH₂CN;        -   —CH(CH₃)CH(CN)₂;        -   —C(CN)₂(CH₂CH₃);        -   —CH₂CH(CN)CH₂CN;        -   —C(CN)(CH₃)CH₂CN;        -   —CH(CH₂CH₃)CH₂CN;        -   —CH(CN)CH₂CH₂CH₃;        -   —CH(CH₃)CH₂CH₂CN;        -   —CH(CH₂CN)CH₂CH₃;        -   —CH(CH₃)CH(CN)CH₃;        -   —C(CN)(CH₃)CH₂CH₃;        -   —CH₂CH(CH₃)CH₂CN;        -   —C(CH₃)₂CH₂CN;        -   —CH(CN)CH(CH₃)₂;        -   —CH₂CH₂CH(CN)CH₃;        -   —CH₂CH(CH₂CN)CH₂CH₃;        -   —C(CH₃)(CH₂CH₃)CH₂CN;        -   —CH₂CH₂CH(CN)CH₂CH₃;        -   —CH(CH₃)CH(CN)CH₂CH₃;        -   —CH₂CH₂CH₂CH(CN)CH₃;        -   —CH(CH₃)(CH₂CH(CN)CH₃;        -   —C(CH₂CH₃)₂(CN);        -   —CH₂CH₂CH(CH₃)CH₂CN;        -   —CH(CH₃)CH(CH₃)CH₂CN;        -   —(CH₂)₂C(CH₃)₂CN;        -   —CH(CH₃)C(CH₃)₂CN;        -   —CH(CH₂CH₃)CH(CN)CH₃;        -   —CH₂CH(CH₃)CH₂CH₂CN;        -   —C(CH₃)₂CH₂CH₂CN;        -   —CH(CH₂CH₃)CH₂CH₂CN;        -   —CH(CH₂CN)CH₂CH₂CH₃;        -   —CH(CN)CH₂CH₂CH₂CH₃;        -   —CH(CH₃)CH₂CH₂CH₂CN;        -   —C(CH₃)₂CH(CN)CH₃;        -   —C(CH₃)(CN)CH(CH₃)₂;        -   —CH(CH₂CN)CH(CH₃)₂;        -   —CH₂CH(CN)CH₂CH₂CH₃;        -   —C(CH₃(CN)CH₂CH₂CH₃;        -   —CH₂CH(CN)CH(CH₃)₂;        -   —CH(CN)CH₂CH₂CH₂CH₃;        -   —CH₂CH(CH₃)CH(CN)CH₃;        -   —CH(CN)CH₂CH(CH₃)₂;        -   —CH(CN)CH(CH₃)CH₂CH₃;        -   —C(CH₃)(CN)CH(CN)CH₂CH₃;        -   —C(CN)(CH₂CH₃)CH(CN)CH₃;        -   —CH(CH₂CN)CH₂CH₂CH₂CN;        -   —CH(CN)CH₂CH₂CH₂CH₂CN;        -   —CH₂CH(CN)CH₂CH₂CH₂CN;        -   —C(CH₃)(CN)CH₂CH₂CH₂CN;        -   —C(CH₃)(CH₂CH₃)CH(CN)₂;        -   —C(CN)₂CH(CH₃)CH₂CH₃;        -   —C(CN)₂CH₂CH(CH₃)₂;        -   —CH(CH(CN)₂)CH(CH₃)₂;        -   —C(CN)(CH₂CH₃)CH₂CH₂CN;        -   —CH(CH₃)CH(CN)CH₂CH₂CN;        -   —CH₂CH(CN)CH₂CH(CN)CH₃;        -   —C(CN)(CH₃)CH₂CH(CN)CH₃;        -   —(CH₂)₃CH(CN)CH₂CN;        -   —CH(CH₃)CH₂CH(CN)CH₂CN;        -   —CH(CH₂CH₃)CH(CN)CH₂CN;        -   —C(CN)(CH₂CN)CH₂CH₂CH₃;        -   —C(CH₃)₂CH(CN)CH₂CN;        -   —C(CN)(CH₂CN)CH(CH₃)₂;        -   —C(CH₃)(CH₂CN)CH₂CH₂CN;        -   —CH(CH₂CN)CH(CH₃)CH₂CN;        -   —CH₂CH(CH₂CN)CH₂CH₂CN;        -   —CH₂CH(CH₂CN)CH(CN)CH₃;        -   —C(CH₃)(CH₂CN)CH(CN)CH₃;        -   —CH(CH(CN)₂)CH₂CH₂CH₃;        -   —C(CN)₂CH₂CH₂CH₂CH₃;        -   —CH(CH₂CN)CH₂CH(CN)CH₃;        -   —CH(CH₂CH₂CN)CH(CN)CH₃;        -   —CH(CH₃)CH₂CH₂CH(CN)₂;        -   —CH(CH₂CH₃)CH₂CH(CN)₂;        -   —CH₂CH(CH₃)CH₂CH(CN)₂;        -   —C(CH₃)₂CH₂CH(CN)₂;        -   —CH₂CH₂CH₂C(CN)₂CH₃;        -   —CH(CH₃)CH₂C(CN)₂CH₃;        -   —CH(CH(CN)₂)CH(CH₃)₂;        -   —CH₂CH₂CH(CH₃)CH(CN)₂;        -   —CH(CH₃)CH(CH₃)CH(CN)₂; and        -   —CH₂CH₂CH₂CH₂CH(CN)₂ and combinations thereof.    -   13. The fluorosilicon nitrile compound of claim 12, wherein the        fluorosilicon nitrile compound contains, as substituents        attached to the silicon atom, one fluorine atom, one cyanoalkyl        group, and two C1-C8 alkyl groups, which are the same as or        different from each other.    -   14. The fluorosilicon nitrile compound of claim 13, wherein the        fluorosilicon nitrile compound contains, as substituents        attached to the silicon atom, two alkyl groups selected from the        group consisting of methyl, ethyl, n-propyl, iso-propyl,        n-butyl, sec-butyl, iso-butyl, tert-butyl and combinations        thereof.    -   15. The fluorosilicon nitrile compound of claim 12, wherein the        fluorosilicon nitrile compound contains, as substituents        attached to the silicon atom, two fluorine atoms, one cyanoalkyl        group and one C1-C8 alkyl group.    -   16. The fluorosilicon nitrile compound of claim 12 or 15,        wherein the fluorosilicon nitrile compound contains, as        substituents attached to the silicon atom, two alkyl groups        selected from the group consisting of methyl, ethyl, n-propyl,        iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl and        combinations thereof.    -   17. A fluorosilicon nitrile compound of general formula        Si(R¹)(R²)(R³)(R⁴), wherein one or two of R¹-R⁴ are fluorine        atoms, one or two of R¹-R⁴ are cyanoalkyl groups, which are the        same as or different from each other where two cyanoalkyl groups        are present, and the remaining R¹-R⁴, if any, are alkyl groups;        subject to the proviso that the fluorosilicon nitrile compound        is not SiF₂(CH₃)(CH₂CH₂CH(CN)CH₃; SiF₂(CH₃)(CH₂CH₂CH₂CN);        SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); or SiF₂[CH₂CH(CH₃)CH₂CN]₂.    -   18. A method of making a fluorosilicon nitrile compound in        accordance with any one of the preceding claims, wherein the        method comprises reacting a chlorosilicon nitrile compound with        a fluorinating agent under conditions effective to exchange        fluorine atoms for the chlorine atoms in the chlorosilicon        nitrile compound and wherein the chlorosilicon nitrile compound        has a total of four substituents attached to a silicon atom,        wherein one or two of the substituents are chlorine atoms, one        or two of the substituents are cyanoalkyl groups, which may be        the same as or different from each other, and the remainder of        the substituents, if any, are alkyl groups, which are the same        as or different from each other.    -   19. The method of claim 18, wherein the fluorinating agent is        selected from the group consisting of HF, MF, MHF₂ and SbF₃,        where M is Na, K, Rb, Cs or NH₄.    -   20. The method of claim 18 or 19, wherein the chlorosilicon        nitrile compound is prepared by hydrosilylation of an alkene        with a chloroalkylsilane.    -   21. The method of claims 18 through 20, wherein the alkene is a        cyanoalkene.    -   22. A method of making a fluorosilicon nitrile compound in        accordance with any one of the preceding claims, wherein the        method comprises hydrosilylation of an alkene with a        fluoroalkylsilane.    -   23. The method of claim 22, wherein the alkene is a cyanoalkene.

Within this specification embodiments have been described in a way whichenables a clear and concise specification to be written, but it isintended and will be appreciated that embodiments may be variouslycombined or separated without parting from the invention. For example,it will be appreciated that all preferred features described herein areapplicable to all aspects of the invention described herein.

What is claimed is:
 1. A method of making a fluorosilicon nitrilecompound comprising reacting a chlorosilicon nitrile compound with afluorinating agent selected from the group consisting of HF, MF, MHF₂where M is Na, K, Rb, Cs or NH₄, SbF₃, ZnF₂, PbF₂, Hg₂F₂, AgF₂, CoF₂,CuF₂, WF₆, NaBF₄, mixtures of NaF and H₂SO₄, BF₃, BF₃ etherates,Na₂SiF₆, NaPF₆, NaSbF₆, NaBF₄, Me₃SnF, PF₅, PhCBF₄, NOBF₄, NO₂BF₄, KHF₂,NH₄HF₂ under conditions effective to exchange fluorine atoms for thechlorine atoms in the chlorosilicon nitrile compound and wherein thechlorosilicon nitrile compound has a total of four substituents attachedto a silicon atom, wherein one or two of the substituents are chlorineatoms, one or two of the substituents are cyanoalkyl groups, which maybe the same as or different from each other, and the remainder of thesubstituents, if any, are alkyl groups, which are the same as ordifferent from each other.
 2. The method of claim 1, wherein thechlorosilicon nitrile compound is prepared by hydrosilylation of analkene with a chloroalkylsilane.
 3. The method of claim 2, wherein thealkene is a cyanoalkene.